


Everything But

by ImpalaDreams (impaladreams)



Category: Supernatural
Genre: Choose Your Own Adventure, F/M, First Time, Impala Sex, Loss of Virginity, Plot What Plot/Porn Without Plot, Virginity
Language: English
Status: Completed
Published: 2014-03-16
Updated: 2014-03-16
Packaged: 2018-01-15 21:37:30
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 8,726
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1320055
Author URL: https://archiveofourown.org/users/impaladreams/pseuds/ImpalaDreams
Summary: <blockquote class="userstuff">
              <p>When you find out you're working a dragon case with the boys, you'll have to pick which one to go after to take your virginity. (Basically a choose your own adventure pwp one-shot.)</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> I started writing this as a Dean imagine but kept wondering what would happen if the reader went with Sam. Basically you'll get to choose Sam or Dean after the opening. Or what the hell, read both. I'm not judging.

The screen door creaks shut behind Dean as he strolls into the cabin and throws his keys on the table. "It's dragons," he announces.

He flops down on the couch next to you. Sam clicks off the tv from his vantage point at the table on the side of the room. "You sure?"

"Definitely all virgins," Dean says, giving a crooked suggestive grin.

Your stomach drops. You're suddenly glad you didn't take that thirty mile drive with him to play FBI with the locals.

"Well at least we have this," Sam says reaching down into a duffel bag at his feet and pulling out a mason jar full of congealed red liquid. He palms the jar and crosses the room, slinging the bag over his shoulder. "I better get a move on though. If I drive all night I can be at Greg's by tomorrow morning." Greg is a hunter and metal worker and has promised to help fashion some new dragon slaying swords. 

"So, question?" you venture. "What exactly is a dragon's definition if virginity? Are we talking Bill Clinton, gotta be P in the V, or does like, third base count?"

Sam shrugs. "Well, traditional views of virginity would suggest any sort of sexual contact like oral sex would, uh, count so to speak," he answers.

Dean shakes his head and tsks at his little brother, sitting up somewhat. "Are you saying you wouldn't treat a girl who's done 'everything but' as a virgin?" Dean asks.

Sam thinks for a moment. "No...I guess you're right," he responds You shift uncomfortably. "Wanna come see some swords forged, Y/N?" he asks you with a grin, grabbing Dean's recently discarded keys.

**Choose:**

[Stay at the cabin and spend the night with Dean. (Ch. 2)](http://archiveofourown.org/works/1320055/chapters/2746159)

[Go on the overnight trip with Sam in the Impala. (Ch. 3)](http://archiveofourown.org/works/1320055/chapters/2746180)


	2. Dean

You are dying a little bit internally. There is nothing more you want than to go watch Greg make you all blades forged from the blood of the last dragons they'd killed. But you've known this was a possibility since taking the lead with them. You've already made your choice. And it isn't Sam.

"No, I think I'll stay here. But thanks though." You feel disappointment creep over you because you know how cool that's going to be.

"Suit yourself," he shrugs, heading to the door. "See you sometime tomorrow afternoon. We should be ready to go tomorrow night," he says to Dean.

Dean nods and you wave goodbye. "Be careful with my baby!" he shouts and moments later you hear the Impala rev to life again. He turns his attention over to you, a bored look playing on his face. The evening sun is streaming in through the window and playing beautifully off his features, highlighting his green eyes, tanned skin and the lighter tones in his hair. You consider just making your move but then he opens his mouth. "Wanna play poker?"

Several whiskeys and a couple dozen hands later, the sun has set and you're both still sitting across from each other at the small table. Your pile of chips is dwindling and you're grateful you're not playing with real money. You learned pretty quickly not to bet real money with the boys.

"All in," Dean says, pushing his chips in.

"What?!"

"You're bluffing," he says. "Your nose always twitches when you try not to laugh when you bluff." He watches you in amusement as he explains. You wrinkle your nose and fold your cards, face down, so he doesn't see the off suited two and four. "And for the record, you clench your jaw when you have a good hand."

Well, someone sure had been watching closely. Attention to detail. You smile. He takes his winnings and begins to shuffle the cards again. Now is your best chance to make a move. "So I've been thinking about the hunt and if there was a risk factor for us, you'd want to fix it, right?"

"Yeah, course," Dean says idly, more focused on shuffling than what you're saying. "Why?"

"I need you to fuck me."

The cards he's shuffling become skewed and you know at least you have the upper hand here, even if you suck at poker. "Excuse me?" he asks, laughing slightly and looking at you like he's not sure if you're joking or he misheard you.

"Well, you and Sam both seem to be in agreement that 'everything but' wouldn't really count." He refills his glass with a heavy pour from the bottle between you on the table and gets up, starting a slow pace across the room as he sips. You know he's in thinking mode and you kick yourself for even having this discussion. You should have just gotten drunk with him and gone for it. Now he's over analyzing the situation.

"You'll stay here then. Sammy and I should be able to handle them and then you won't set off their virgin alarms or whatever," he says.

You laugh loudly. "Yeah right! And miss fighting DRAGONS? Dragons, Dean! How many people can say they've slayed a dragon?" He raises his eyebrows and you see the corners of his mouth twitch. You're not sure if it's because of your enthusiasm or because you know he's fought dragons before, but either way you're winning him over. "Besides, we know there are at least two. Why intentionally hurt your chances when we can go in with them outnumbered?"

He sighs, quits his pacing, and sits down on the couch. He runs a hand over his face and you get up to go sit next to him. "Listen, maybe you should talk to Sammy about this. He's better at the chick flick, devirginizing stuff than I am. I don't do virgins." He takes another gulp of his drink and you're pretty sure it's just so he doesn't have to look at you.

"Alright, I'm going to ignore the part where you just tried to pimp me out to Sam. But really, Dean? Don't you think I've weighed my options?" He gives you a confused stare, brows coming together as he looks you over. "I'm sure that Sam's technique is perfectly adequate, but I've shared a bedroom wall with him and..." You pause, remembering the last night he'd spent with a woman, his dominant growling moans and her keening cries and the relentless banging of the headboard "...I just think I'd prefer you." He gives you a look, not full on Winchester eye sex, but it's definitely more flirtatious than you've seen since this conversation started. You move a little closer to him and he picks up the whiskey glass to drink again. You lips are by his ear when you whisper, "Besides, you're the hot one."

A slow blush creeps into his cheeks as he lowers the glass and you know it's not just the alcohol. Oh, you will savor the moment that you made Dean Winchester blush while asking HIM to take YOUR virginity.

He turns to face you and now your lips are within kissing distance and you have to refrain. He lets a hand travel to the side of your face, thumb grazing over your cheek before he brushes a stray strand of hair behind your ear, fingers lingering by your jaw. "Your first time should be with someone special, Y/N." He squints at you seriously and you can see the heartbreak behind his eyes.

He pulls his hands away with determination and downs the rest of his drink. He makes a move to get up and you know he's going for more whiskey so you pull him back. He places the empty glass on the table with a resigned sigh before facing you again. His eyes look so full sadness. You were completely preoccupied with taking care of this, you hadn't stopped to think that maybe it would mean something more to him. "Dean," you say, returning his hurt look. "You are special."

He scoffs and looks away, eyes wandering to the table where the bottle still rests. This time it's your hand on his cheek as you turn his face to you once more. "I want you, Dean." He shakes his head to the side, trying to draw himself away but catches your gaze. His eyes trace your features and his mirrored longing is evident. He leans closer and you lick your lips. "C'mon," you whisper. He's just millimeters away from you and you can smell the lingering scent of liquor ghosting across his breath. "You're not going to make me beg, are you?"

You see that sexy grin and hear him mutter, "Yeah, I am," right before his lips meet yours. His lips are warm and soft and gentle as they place exploratory kisses to your mouth. You kiss back and enjoy the feel of his full lips pressed against yours. He parts his mouth and you feel his tongue dance across your lower lip. You grant him access as you shift so you're in his lap, straddling him on the couch. Your tongues meet at the same time his hands find your hips and you wrap your arms around his neck. His kisses are turning you on and you press your heat down into his growing erection. He lets out a short, low groan and briefly breaks the kiss.

"So...everything but?" he questions, somewhat mockingly. His fingers are at the hem of your shirt and you can feel them start to graze the skin at your stomach, working their way up until he's pulling it off. He makes quick work of his own t-shirt. The sight of his naked chest and muscled arms makes your insides twist with desire. He's kissing your chest, just above your bra where your breasts are threatening to spill over. You run a hand through his hair and grind against him harder, his grip on your hips tightening to pull you even closer to his erection. "Damn, baby," he says looking up at you.

He's flushed with arousal and you sense that it's probably been a while for him. You want this to last though. "How about I show you some of the everything?" you say into his ear as you continue to work your hips against him. He groans in response and you take that as a yes. You slink to the floor in front of him, guiding his hips a little closer to the edge of the couch for better access as you undo his fly. He helps you push his jeans and boxers off, finally discarding them on the floor so he's naked in front of you.

You run your hands teasingly up his thighs, making him shiver before you take his long cock in your hand. Holding the base, you begin to lick long strokes with your tongue up his length. You tease the underside before doing the same to the sides and repeating, this time letting your lips start to graze over him as well. "Fuck..." he curses breathily above you. You see a few drops of precum leaking from his tip and move your tongue to lick them up, tongue swirling around the pink head before sucking it into your mouth. You stroke his length, still slick with your spit, as you massage the sensitive tip of his dick with your tongue.

Above you, Dean let's out a desperate moan and you can tell from the way both his cock and hips are twitching that he's trying very hard not to buck into your mouth. You reward the effort by taking more of him in your mouth, hollowing out your cheeks to suck him in, mouth moving up and down a few more inches of cock. "Yesss," he hisses out, spreading his legs a bit more to give you better access, hoping you'll swallow down more of his long dick. You devilishly pull away though making him whimper at the loss of your mouth. The sound is replaced with a lower, throatier moan as you begin to jerk his cock and lower you mouth to his balls. Your hand works over him as you suck one of his balls into your mouth running your tongue over the smooth skin. For a hunter, Dean was certainly well groomed. His sac tightens when you move your mouth to the other ball, your wrist twisting your palm over the head of his dick. You vaguely register his head rolling to rest on the back of the couch.

You pull your mouth away to switch places with your hand, cupping his balls as you swallow him down, further than you had before. "Oh fuck, holy shit, Y/N!" He starts to grind into you, instinct and reflex taking over, and you slide your hands to his hips holding him down while you open your throat to swallow more of him. "I'm gonna come," he moans loudly, eyes casting down on you and meeting your gaze. You smile around his cock, tongue and mouth working his length harder. "I can't, babe, I'm gonna..." You open your throat and take him as he moans out his climax above you. You feel Dean's cock twitch with release and the sticky, salty slide of cum down your throat. He's shaking and moaning above you, fists gripping the edge of the couch by your head.

You pull you mouth off him but let your tongue linger to lap the last of his orgasm that your hand jerks out.

"Fuck!" He curses again, throwing his head back. You lick your lips. "Virgins are not supposed to suck dick like that," he gasps out. He smiles and takes a few panting breaths and you look up mirroring his grin. "C'mere," he says, pulling you up.

You follow the lift of his hands moving back on the couch to straddle his hips again. He brings his lips crashing to yours and you're swallowed up by his kisses and his hands running all over you. He kisses you softly, almost sweetly, as his hands graze up your back, fingers coming to rest on your bra clasp as he expertly unhooks it and his hands slide to your shoulders to push the material away. His hands return to your back though instead of groping you, and you sigh as you feel him pull you down to him, skin finally meeting his naked skin and you both moan into his kiss. His strong arms move down to your ass, gripping your still jean clad flesh against him tightly as he stands up suddenly. You grip his shoulders and wrap your legs around his waist to hold yourself up. You squeal slightly in surprise and see him smirk at you as he grips your ass and begins to walk. "What...?"

"I'm not taking your virginity on a couch," he smiles against your neck as he carriers you into his room. His shins meet the edge of the cot like bed and he lowers you to the flimsy mattress, tumbling down on top of you. He kisses your neck and his hands finally find your breasts, massaging and kneading them with his fingers as you arch your whole body up into him. He trails a hand down finally meeting the button of your jeans which he quickly unfastens before pulling your pants down. You kick them off and part your legs, allowing him room to move between them. He lowers his head to suck and lick your nipples while his hands trail up your thighs, finally arriving at the heat in the center. He runs a finger down the middle of your panties, smirking and pulling away as he feels your wetness seeping through, the light gray material of the thong now marked darker with your juices. He hooks his fingers in the waistband of the underwear and pulls them down. When you're naked, he smiles and lays down between your legs. His arms circle under you, resting both of your legs over his shoulders. He teasingly kisses your thighs and you feel his stubble slowly make its way to your center. You sigh in frustration and catch the way he smirks as he pulls your legs tighter around his head and drops his mouth to you. When he speaks you can feel his breath hot on your skin. "Told you I was gonna make you beg." You feel his lips grazing your pussy and he starts to lick you open. Tongue lapping at your folds, licking up your wetness and parting your lips, just grazing by your clit but not nearly enough. You feel yourself get even wetter from his teasing and he seems to notice too as he lowers his head to press his tongue into you. He groans in approval tasting you and you feel his eager tongue tracing across your lips again. When he reaches your clit he gently laps at it with his tongue, teasing the hood back to expose the sensitive bud. He begins too flick his tongue over it, fluttering just the tip over your clit.

You whimper and try to press up into him but he holds you down and continues his teasing assault. His tongue starts to circle your clit, lightly at first and then pressing into you harder with a flat tongue. Your hips are beginning to shake and you feel your juices dripping down yourself and Dean's face. "That feels so good right there, Dean," you moan pushing up into him. He works his tongue faster and you feel your orgasm building. He maneuvers a finger to press inside you, your pussy slick but tight with your legs around his head still. He curves his finger upwards and you feel him curling it into your gspot, pressing wide hard circles to match the motions of his tongue. "Oh! My! God!" you scream. His isn't the first mouth on you but he's turning you on and building you up in an unprecedented way. You feel your climax tightening in your gut and throw your head back as a guttural moan escapes you. "I'm gonna come, Dean," you cry, legs stiffening around his head as your hips press up into his eager mouth. Then you're losing it, shaking and bucking into him, crying out his name in tortured bliss as he continues to lick and rub you through your orgasm.

Before you even stop coming he's sliding another finger inside you, feeling you clench around him as your orgasm lingers. He pulls his mouth away and watches you as he slides his fingers in and out of you. You remove your legs from his shoulders, splaying yourself out on the bed and giving him a better angle to watch from. He scissors his fingers inside you and you feel a new wave, a different kind of pleasure wash over you. "Please, Dean," you gasp. "I want you."

He kisses your thigh, leaving a streak of your juices from his face across it, and adds another finger to your hole. "I want you too." He kisses his way down your open thighs again. "But I want to make sure you're ready for me."

You groan in a mix of ecstasy and frustration as his mouth finds your clit again. He licks over it slowly before closing his lips around it, drawing it into his mouth. You already feel yourself building to another orgasm off the cusp of your last. His three fingers are still working inside you, you feel him graze your gspot before pressing deeper inside you and then repeating the action. His mouth is fixed at your clit, sucking the engorged bud into his mouth where his tongue licks over it, making your moan and shake into his mouth. "That feels...awesome," you sigh out. You hands reach down to hold his head in place, fingers tangling in his short hair as your fingernails gently graze his scalp. "Fuck, Dean, don't stop, you make me feel so good," you cry out. You're right on the edge and look down to see him, eyes shut and face buried in you, working tirelessly to get you off again. Then he fucking moans, low and drawn out and absolutely guttural against you, and you lose it again. Your hips buck up involuntarily and your hands tighten in his hair when your climax takes you suddenly. You're lost in a rush of pleasure, screaming and rolling your hips into him as he works his three fingers harder, pumping them into your contracting, spasming pussy. He doesn't relent, mouth still sucking your clit long after your hands leave his hair to fist the bedsheets at your sides, letting wave after wave of your shuddering orgasm wash over you. He holds you there, still twitching against his mouth as he slows his motions with his tongue, the occasional flick still making you convulse unexpectedly. You whimper at the loss when he pulls his fingers from you. "Please, more," you whine disjointedly.

He smiles, licking his fingers clean before wiping your juices from his face. "You taste really good," he says softly, kissing your neck before you turn face to meet his mouth, kissing him fully and tasting yourself on his tongue still. He positions himself on top of you, propping himself up but not so much that you can't feel his erection pressed against your thigh. You sigh, already sated and pliant for him after his mouth went to town on you, and you spread your legs apart to give him entrance. He takes his dick in his hand and traces the tip along your wetness. You groan in frustration. "Please?" you ask softly.

Dean smirks and lowers his mouth to kiss you, his hardness still sliding across your wet folds. "Please what?" he asks, and you both gasp as the head of his dick makes contact with your clit. You let out a weightier groan. "I told you I was going to make you beg," he reminds you again. You pout in response. He thrusts against you again, his length sliding easily over your slick folds. "Tell me what you want, Y/N."

You arch into him, grinding back against him, desperate to feel him inside of you. "Please, Dean. I want you. I need you to fuck me," you beg.

He teases his head against your clit again, rubbing it into you. "Mmmhmm," he sighs and you feel his breath hot on your ear.

"Please, I want this so badly, Dean." You're practically crying beneath him and gasp as you feel him align with your hole. "I need to feel you in me. I want you to take me. Dean, I want it to be you." As soon as the words leave your lips he begins to sink into you and you both hum eagerly at the sensation.

"You feel so good, baby," he moans in assurance, pressing into you entirely too slowly. "Let me know if it hurts, I'll stop, okay?" He kisses your jawline, hands sweetly cupping a breast, tracing down to grip your hip. Then he's kissing you again, tongue dancing with yours as he pushes into you more firmly, stretching you out and making you whimper in pleasure. "You okay?" he asks, pausing to pull back and examine your features.

"Yes, yes. I'm so good," you confirm. "Please, more, please, Dean!" He leans down to capture your mouth in his as he sheaths himself in you, thrusting in fully. You suck his bottom lip into your mouth, raking your teeth over it as you feel him stretch you wide open and a pulse of pleasure beat through your body. He slides a hand down to thumb your clit and you break away from your kiss, throwing your head back, panting in pleasure. His lips are still by your mouth, following you as your arch into him. He doesn't move much but presses against you, grinding into you. He continues to thumb your clit, kissing your chin and jaw and down your neck as you gasp and arch into him, overwhelmed by the sensations coursing through your body. "You feel..." you pant, pressing against him harder, he's still grinding against you, not thrusting, just pushing and pressing deep inside you. "You're so deep, I feel you..Oh my God..." You feel a tightening in your groin and he moans as rolls his hips into you, finally starting to move, driving you even more crazy. "Dean, I'm so close...I...oh my...yes..."

He grunts and thumbs your clit harder, rocking into you more, he slides almost all the way out before thrusting back in, filling you up again, grazing past your gspot as he hits you deep inside. "Yes, let go, Y/N," he says and your limbs are suddenly around him, gripping his back, legs sliding around his waist, pulling him closer to feel him deep inside you. His thumb presses harder against you and it sends you over the brink. You feel yourself contract around him, the tightening in your groin spilling over and coursing through every nerve ending in your body. You feel him begin to thrust in earnest, withdrawing and pumping back into you, slow and measured and in time with the waves of pleasure already coursing through you. It builds you up even more and you feel another release wash over you, even harder than the last. You're lost in a loop of pleasure, hips instinctively working with his as you vaguely register him moaning and burying his head into the space between your neck and shoulder.

Your legs are shaking around him, hips still thrusting up without your command, clenching, grinding, fucking against him until your senses are so overwhelmed you have to pull his hand away from your clit, gasping in relief as you're able to come down from your release somewhat. You pull his hand to your mouth, sucking his thumb between your lips to taste yourself on him. You hear him groan above you and he angles his hips differently, thrusting down so he's grinding against your clit with his pelvis now. Your legs shake and search for purchase along his hips or back, skin slicking against sweaty skin as he builds your pace. He pulls his hand from your mouth, fingers lacing with yours against the mattress as he holds you down with one hand, the other looping around your waist to draw you to him, thrusting into you hard and deep so that you both cry out in pleasure.

His hand laced with your squeezes tightly. "You feel so good, baby," he moans. Your free hand, not tangled with his, finds the back of his neck, centering you both as your eyes meet. He's staring at you intently and his features are awash with pleasure and awe as you moan and constrict against him. 

He moves with you, pressing, pulling, grinding, and you feel his hips jerk against you. "Dean, I'm going to..."

"Me too," he grunts out and you feel him thrust a little harder, faster, pushing you both to your peak. You shake beneath him, both arms reaching around him to pull him close as you work your hips against him, writhing in a shuttering release moaning his name. "Oh God, Y/N," he cries, lowering his head to bury in your neck and you feel him thrust in you completely, fully, cock twitching in release as he comes inside of you. 

You remain entwined, arms and legs locked together, gently rocking, until long after your orgasms have subsided. He kisses you slowly, hand running from the side of your head, down your neck, over your shoulder, caressing every inch of skin he passes over. "Did you like that?" he asks softly.

You nod and smile at him softly, staring up into his green eyes, returning your satisfied gaze. "Yeah, I did."

"Good. So did I. You know it was a first for me too..."

You give him an incredulous sideways glance and he just smirks and rolls off of you. "You mean you never?"

He wraps his arms around you, pulling you close and spooning up behind you. "I guess you could say you were my first first."

You smile and relax into him, feeling sleep start to creep over you. "Well, I'm glad we both had good firsts." He laughs but it's faint as you both drift off to sleep.


	3. Sam

You look up at Sam, squinting through the sunlight streaming in through the window behind him and making the golden tones in his hair stand out. He licks his lips idly while raising his eyebrows and awaiting your answer. "Yeah," you nod, smiling at him. "Let me just grab a few things." You throw a few essentials from your room, clean shirt, brush, deodorant, a few snacks into your own bag and are ready to join him in no time. Your heart is racing in anticipation not only over the dragon swords but also the trip itself. You're out the door behind Sam in a moment and throw up a wave of acknowledgement when you hear Dean scream, "Be careful with my baby!" from inside the house.

You slide into the passenger's seat which is a rarity since you're usually banished to the backseat on long drives with both of them. Sam is already starting the car and whipping out his ipod, another rarity for any Winchester family road trip. "So how long is the drive?" you ask and he hands you a map and some directions.

"Close to 600 miles. A few states over. Probably be there in about 10 hours." You know that's a conservative estimate given the way both of the guys drive.

Several hours later it's dark and the only light on the country road is the high beams of the Impala. It's the early morning hours and you're both staving off sleep. The only sound is the hum of the engine over the music still playing from Sam's ipod. A comfortable silence has fallen between the both of you that you only break when you see Sam yawn widely and shake his head awake, reaching for his coffee cup which he quickly drains the last of. "How are you still falling asleep?" you ask. "Didn't that have three shots of espresso in it?"

He nods, laughing slightly. "I'm a big guy," he says. "Takes a lot to keep me up." He sounds a bit embarrassed but it's kind of sexy too and you run your eyes over his large frame.

You smile and undo your seatbelt, moving closer to him to whisper in his ear. "Maybe I can help," you say, breath ghosting over his ear at the same time your hand brushes against his groin. He looks at you, quickly, not taking his eyes off the road for long and you see a little smile of understanding pull at the corner of his lips. You move your hand again, this time cupping him through his jeans.

He turns his head again, giving you a quick peck on the lips. "Ok," he says, lowering one of his hands from the steering wheel so he's opened up to you. You grin and start to kiss his neck as your hand starts to work on his fly. He shifts his hips to accommodate your hand which is beginning to fish inside his jeans. On second thought, he raises his hips slightly and you both push his jeans down so they're resting around his thighs and he's exposed to you. He groans when you lower your head to suck down his still only half-hard cock. It's large even though not fully erect and you know it's probably the last time you'll be able to fit it in your mouth as it begins to harden. His free hand that's not on the wheel is tracing patterns along your back and he sighs with pleasure as your mouth and hand find a perfect sequence of motions. "You know how to wake me right up," he purrs out and you feel yourself instantly become wet. His hand moves to grab your ass which is sticking up as you kneel on the bench seat of the Impala next to him. You moan as his hand cups your ass cheek, kneading it in his large hand as you continue to eagerly slurp his cock. When you take him down your throat as far as he'll go, he releases your ass, hand swinging away before crashing back to spank you. You moan around his dick and arch your back, angling your ass up for him. His broad hand spanks your other cheek, fingers gripping your ass through your jeans and massaging immediately after. You pull your mouth away from him to audibly moan after that one. Your hand jerks him off as you suck and lick the head of his cock, looking up at him. He bites his lower lip and groans, squinting at the road and you see his arm raise to spank you again. You gasp in pleasure and his dark eyes cast down on you, meeting your gaze as you run your tongue under the head of his dick. You taste the first drops of precum as he moans loudly and brings both hands to white knuckle the steering wheel. You feel the Impala rev a bit and then hear a familiar little squeal of the breaks.

You feel yourself getting even wetter as you taste him across your tongue and you eagerly suck the head of his cock, hoping for more of that flavor. "Yeah, suck it down again," he moans from above you. He's still intently focused on the road but lowers one of his hands to the back of your head. He doesn't press down but he palms the your head as you sink your mouth down around him again, opening your throat to let him slide down once more. "Fuck, that's it," he encourages, fingers tangling in your hair as he pulls you back slightly. You take him back down again and his hand rests then pulls you back again, starting a slow, needy rhythm. It's too much and you're too turned on. You feel your own juices pooling in your underwear and lower one of you hands to slip inside your jeans. "Yeah, touch yourself for me, Y/N," he says. "I wish I could feel how wet that pussy is getting with my dick down your throat." He thrusts up to meet your mouth as if to make a point, his insistent hands still on your head, not forcing but certainly commanding. You moan around his dick not just at his words but also because your fingers have found your clit and are rubbing quick circles against it in your tight jeans. You relax and let him move your head for you, guiding your mouth up and down his dick, thrusting his hips up slightly. You hear the Impala engine roar and realize you're going faster than you have been. "Yes, yes, Y/N!" he moans. "I'm going to come down your throat." You let out one last moan around his fat cock as he twitches and screams his release, cock pumping into your throat as you suck down his juice.

Even after he's finished his cock is still large as his erection dissipates slowly. You clean him with your mouth as he tries to catch his breath above you, still panting hard from his orgasm. You sit up just as he begins to slow the vehicle, pulling off the road and into a small clearing of trees, probably an abandoned police speed trap locale. He puts her in park, turns the engine off and faces you immediately and pulling you to him for a kiss. His tongue is almost instantly in your mouth, pressing against yours and licking his own taste from your mouth. He bites at your lower lip as he pulls his lips away slowly from yours. "That was so hot, Y/N," he breaths out, still panting and exposed post climax.

You run your hands through his hair, biting your lip in slight embarrassment as you nod in agreement. "Sam?" you ask. He looks up at you with puppy dog eyes, happy half grin on his face. "I need to have sex with you before we fight the dragons tomorrow." You blurt it out and it comes out as big long word that takes him a moment to decipher.

He grins a little wider then furrows his brows slightly in confusion before his eyes widen in realization. "Oh my God," he says pulling back and turning away from you. "I'm so sorry." He spares you a quick look and his face is painted with regret. You begin to mentally kick yourself. Of course Sam is going to back out of this. It's even more if a tragedy because you're so turned on. "If I had known I wouldn't have," he gulps, "I'm sorry. I would have cooled it with the spanking and face..." he pauses "fucking." He looks at you again apologetically.

"Why?" you ask, smirking toward him. "I liked it. And besides, it's not like I'm completely inexperienced."

He nods slowly in understanding. "Ah, the 'everything but' question," he says. You raise your eyebrows pointedly, letting him know he's right. "You know you could have stayed home and," he starts, not quite sure how to finish that sentence. He rolls his eyes as he always does when Dean does something predictable. "He would have made a move."

"I know," you say nonchalantly, like it isn't a big deal you know you could have let his older brother fuck your virginity away instead. "And yet here I am in this stinky, old car making a move on you."

He kisses you again, mouth hungry, needy and tongue seeking out yours. "Backseat. Now," he orders and you quickly climb out your door, meeting him in the backseat. His mouth is on yours again, massaging his lips into yours as he unbuttons his own shirt, peeling it off before reaching out to yours. He goes to kiss you again but pulls away cursing instead. "Fuck!"

"What?" you ask, suddenly alarmed and watching him rub a frustrated hand over his forehead.

"I don't have a condom," he says. "I wasn't exactly expecting..." he trails off, eyes leaving yours to trail greedily over your breasts still mostly hidden by your bra.

"I actually..." you feel a bit embarrassed but confess anyway. "Last week when I was supposed to be canvassing I went to a clinic instead to get a prescription for birth control," you admit. 

"I knew you didn't go to those houses!" he immediately says, laughing a bit, sliding in closer to you again knowing he can proceed. He kisses you gently before pulling away and looking at you with admiration. "Wait, have you been planning this?" he asks.

"Maybe," you shrug, fighting back your own smile.

"With me?" he asks again, as if wondering, still, why you didn't stay home with Dean.

"Yes!" you say rolling your eyes. "God! Now can we do this already?" You smile at him suggestively and take off your own bra.

He doesn't need further invitation as he kisses you again and lays you down along the backseat of the car, his own large limbs crammed in next to yours. His hand begins to trail down you from your neck, grazing over your collarbone and down to your breast where it lingers to cup and squeeze. His mouth trails the same path placing tiny wet kiss that his tongue laps over until his lips are closing over your nipple. He sucks and tongues it to a peak while his hand travels lower to undo your jeans. His mouth switches breasts and he doesn't falter as he pushes down your jeans and underwear in one motion. You help him by kicking them the rest of the way off and he adjusts your position. Drawing his lips away from your tits, he brings one of your legs to rest over his hip and he pushes the other away so you're splayed out, one foot resting by the window the other on the floor of the Impala, with him on his side next to you.

He kisses your neck again, tongue working a spot just behind your ear that makes you whimper into his touch. His hand runs up your thighs, approaching your heat and you can feel him smiling against your skin as he draws nearer and you shake with anticipation. You both give a satisfied little groan when his fingers find your wetness and trace the folds of your pussy with the sticky juice. He's biting his lip again and looking at you intensely.

"What?" you half ask, half moan, knowing he's keeping his thoughts from your virgin ears. "I want to know what's going on in that dirty, pretty head of yours."

His fingers connect with your clit and start tracing teasing delicate circles across it. "I was just getting turned on by the fact that your pussy is even wetter than I imagined." He rubs your clit harder pressing into it more with two fingers and eliciting a long drawn out moan from you. "And every time you moan like that, it goes straight to my dick," he whispers dirtily in your ear. His fingers are really moving now and you feel your arousal clenching in your belly and you don't hold back any moans knowing it's turning him on so much. You feel the familiar build, arousal still coursing through you from the activities in the front seat. You're on the edge in no time with Sam's expert hand on you.

"I'm gonna come, Sam," you moan, pressing your hips into the seat as you spread your legs further and he rubs you even harder.

"Yeah, I want that virgin pussy to come for me," he grunts into your ear as you lose it, body shuddering in orgasm. You spasm and shake below him, your hips jerking up into his hand as he watches you ride out your climax. His hand slows only as your hips do and he leans down to kiss you as your regain your breath. His hand is still exploring your pussy though and he lowers a finger down to experimentally press into your opening. You're slick with arousal and he pushes his middle finger up and into you easily, flicking it over your gspot once inside. You groan needily below him pressing yourself into him and he swallows any other sounds with his mouth over yours. He pulls back, adding another finger to press into you and you feel him stretching you out. "You feel so hot and wet against just my fingers, I can't wait to feel your pussy stretched over my dick." You moan, clenching at his words and you feel yourself get wetter around his fingers. "It turns you on when I talk dirty? I can feel your pussy tightening around me."

"Yes, oh my God, yes!" you affirm. Between his filthy mouth and the way his two fingers are pressing and twisting into your gspot you feel like you're read to explode. You need more though and you press against the air, looking for friction that isn't there. "Please," you moan into his neck.

His other arm is pinned underneath you, supporting your head like a pillow and propping him up. "Put your fingers in my mouth," he says, not missing a beat, continuing to stroke his fingers inside you. You obey, bringing your hand to him and he lowers his head to suck one then two into his mouth. He makes a dirty show, tongue swirling around and hollowing out his cheeks to really suck on them, getting them wet with his spit. He pulls away and starts to ease a third finger inside you. "Rub your clit while I finger you and get you ready for my dick," he says looking down to find your hand already working on yourself.

He slips in a third finger and you feel him pressing, stretching you further than you've been before. His fingers are large but you know his cock is even wider. You moan loudly at the thought and your fingers pick up the pace, hips bucking down on his hand. His bicep tenses as his fingers thrust into you harder. At your side, you feel his erection pushing into your leg and slide your free hand down to jerk him off in time with your fingers rubbing your clit. "Yeah, feel my thick cock in your hands. I can't wait to stretch you open and fill you with it." You moan louder and feel yourself tighten around his fingers again. He curls his fingers up, pressing insistently on your gspot. "You're so slick and wet against my hand," you moan loudly and rub your clit harder, "you feel so good clenching and tightening around me," you feel yourself spasm involuntarily around him, "I'd be happy just to fuck you with my fingers all night." He pumps his three fingers into you harder as if to prove just how much he likes fingering you. "Bet I could make you come lots just with my hands. But I'm gonna fuck you so good no dragon will want to come near you."

You move your fingers in faster circles on your clit and turn your head to moan against his neck, whimpering and panting. You're right on the edge, legs shaking and hips thrusting back against him. "I want more than your hands," you reply and he captures your lips with a groan as you moan up into him, releasing again against his hands. You moan and shake against him, pleasure coursing through you once again as both of you bring you to orgasm. Your hand not on your clit is still squeezing and pumping his dick, hand gripped tightly around his erection as your climax racks your body. Neither of you cease your actions until you're panting in exhaustion and both of your hands go limp.

He draws his fingers out of you, and you vaguely register his hand gripping his own dick, fingers slicking your wetness over his own length. He's still kissing you, trailing his lips away from your mouth to softly kiss into your neck. "I want you," he whispers against your ear and it makes you shiver in anticipation. His hands are drifting over your legs, closing them and drawing your body to his. “But I don’t want to hurt you,” he says. Your pliant and let him pull you on top of him, turning around in his arms as he shifts to lie on the seat below you. He pulls you down to him, kissing you slowly, tongue sliding gently against yours as one of his hands tangle in your hair, the other gripping your ass and grinding you against him. You register his hard cock pressed against your pussy and push your hips against him, dripping your wetness onto him. You both moan and he rolls his head back when your clit connects with the sensitive head of his dick. He grips himself with one hand, his other hand holding your hip, and positions you over his member. "Just take it as you can, nice and slow," he whispers, his large head pressing against your opening. "And if it's too much, that's okay," he says sweetly, looking up at you earnestly. "We can stop."

You both moan as you begin to sink down, his head entering you easily and you slow your motions when you feel his thick shaft start to stretch you out. You feel a slight stinging and start to question your ambition, when it's soothed away by his finger flicking over your clit. You feel yourself grow wetter and open up for him as you sink lower, encouraged by his motions against your clit. His finger continues to swirl against your aroused bud and you feel him pressing deeply inside you. You both gasp in pleasure as you take the rest of him, surrounding him completely and groin flush with his. You moan loudly and feel your pussy clench around his thickness when his finger rubs your clit harder. "What? No, dirty thoughts at that?" you tease him.

He looks up at you, smile playing at the corner of his mouth. "No," he says, flicking his finger a bit differently and making you arch and grind against him as you continued to adjust to his length and girth. He trails a hand up your stomach and over your breast. "No, I just think you're really beautiful like that," he says. You feel your hips rock involuntarily and know you want more. He smirks a bit and bites his lip, pulling you down to kiss your lips again, hands finding your hips and guiding you. "Nice and slow," he says, kissing your ear as he whispers. Your hips follow his hands, moving up and off of him before taking him back down. He shifts and angles you a bit differently and you cry out in pleasure as your clit grinds against his dick. You thrust harder, enjoying the friction of his shaft against your clit, the walls of your pussy gripping his dick tightly. He feels you getting more into it and moves a hand to grip your ass as you ride him, groaning out his own pleasure as you speed your actions. "I was afraid of tearing you up if I fucked your tight pussy," he whispers dirtily and you feel him thrusting up to meet your motions. "But you're a natural." You meet him thrust for thrust and you feel the familiar tension starting to build at your center. You choke out a moan as you grind against him harder. "You feel good? You like that?" he asks unnecessarily as the pleasure in his face is mirrored across yours.

You brace yourself on his shoulders, moving faster against him and moaning loudly at his words. "Yes, your so big, Sam. I feel you stretching me out so wide, feels so good," you say. You collapse against him, still moving your hips but losing yourself in the pleasure. You begin to shake around him when he lowers a hand to your center to stroke his thumb over your clit again. "Yes! Oh my God! Sam!" you cry, fucking him harder. He continues to thumb your clit as he rock back against you, thrusting up into you and hitting your gspot as your grind against each other. You feel yourself begin to shudder around him and he's moaning loudly beneath you.

He holds you closer, pumping into you faster as you let your orgasm wash over you, pussy tightening to grip his dick and making him throw his head back in ecstasy. "That feels so good, girl, yes, yes, come around my dick, keep riding it, just like that," he gets out before he's shouting out at his own release. For a moment you're both lost, moaning each others names against the others lips as your bodies lock together and shake in climax. You rock against Sam as your bodies spasm in unison, riding every wave of your orgasms with each other. "You feel so good, you feel amazing," he's still whispering in your ear as you both come down from your climax. You're both out of breath and press your foreheads together stealing the occasional kiss through your labored breaths. You feel him going soft and move from your position straddling him but still lying on top of him.

"That was..."

"Yeah..." he says. He takes a deep breath and then yawns deeply.

"Guess I didn't really help in the keeping you awake bit," you lament.

"I'm not complaining," he says and you can hear the smile in his voice. "Besides, I don't think we'll be too welcome showing up at six in the morning. Let's take a nap for a couple hours, then hit the road again."

You nod against him, already feeling sleep overtake you. You nuzzle into his neck and feel him place a kiss to your head as he wraps his strong arms around you. You were definitely happy with your choice.

**Notes for the Chapter:**

> Really? You picked Sam? Brave choice...


End file.
